4-methylnaphtho[1,2-d]oxazole | 1276119-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methylnaphtho[1,2-d]oxazole
• 英文别名: 4-Methylbenzo[e][1,3]benzoxazole
• CAS: 1276119-00-6
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: QOXJDQFCJQQJOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-5-(1-phenylprop-1-en-2-yl)oxazole 在 碘 作用下， 以 苯 为溶剂， 反应 20.0h， 以66%的产率得到4-methylnaphtho[1,2-d]oxazole
  参考文献：
  名称：

  Photochemical Approach to Naphthoxazoles and Fused Heterobenzoxazoles from 5-(Phenyl/heteroarylethenyl)oxazoles

  摘要：

  A new synthetic approach is presented for the synthesis of naphthoxazoles and fused heterobenzoxazoles. The starting 5-(aryl/furyl/thienyl/pyridyl ethenyl)oxazoles are prepared from the corresponding alpha,beta-unsaturated aldehydes using Van Leusen reagent in very good yields and are transformed into naphthoxazoles and fused heterobenzoxazoles on irradiation under aerobic conditions and in the presence of iodine.

  DOI：

  10.1021/jo1025942

文献信息

• Antiinflammatory and Antiproliferative Activity of Naphthoxazole, Fused Hetero-benzoxazole and Bridged Benzobicyclic Photoproducts
  作者：Ivana Šagud、Ana Ratković、Matea Cedilak、Martina Bosnar、Vanja Kelava、Irena Škorić

  DOI：10.5562/cca3530

  日期：——

  Biological activity of naphthoxazoles, fused hetero-benzoxazoles and benzobicyclo[3.2.1]-derivatives was investigated in proliferation and inflammation based assays. The tested compounds were prepared by photocylization or photocycloaddition reactions. Effect of compounds on proliferation of several cancer cell lines was determined by measuring cell metabolic activity through time. Lipopolysaccharide (LPS) stimulation of peripheral blood mononuclear cells (PBMC) was used to investigate antiinflammatory properties of the compounds. Several naphthoxazoles and fused hetero-benzoxazoles inhibited TNFα protein expression in LPS stimulated PBMC, indicating possible antiinflammatory role which would be interesting to further investigate. Physico-chemical properties of tested compounds have been also studied using chromatographic lipophilicity measure, chrom logD and logP was calculated as the importance of physico-chemical properties of compounds at early stage of discovery of new drugs is well established. The similarities in structure and activity of some representative compounds affirm the need to further address their antiinflammatory properties.

  研究了萘氧唑类化合物、融合的杂环苯并噁唑类化合物和苯并双环[3.2.1]-衍生物在增殖和炎症性实验中的生物活性。经过光环化或光环加成反应制备了被测试的化合物。通过测量细胞代谢活性来确定化合物对几种癌细胞系增殖的影响。使用脂多糖（LPS）刺激外周血单核细胞（PBMC）来研究化合物的抗炎性质。几种萘氧唑类化合物和融合的杂环苯并噁唑类化合物抑制了LPS刺激的PBMC中TNFα蛋白的表达，表明可能具有抗炎作用，值得进一步研究。还研究了被测试化合物的理化性质，使用色谱疏水性测量，计算了色谱logD和logP，因为在新药物发现的早期阶段，化合物的理化性质的重要性已经被确立。一些代表性化合物在结构和活性上的相似性证实了有必要进一步探讨它们的抗炎性质。